Preparation of 1-tosyloxy-4-substituted-2-butenes using Ag(I) salts

Tetrahedron Letters

Volumn 56, Issue 30, 2015, Pages 4480-4482

  Stehouwer, Jeffrey S ^a   Goodman, Mark M ^a  

^a EMORY UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

Fluorine 18; Fluorobutenyl tosylate; N Fluorobutenyl nortropane; Positron emission tomography

Indexed keywords

NORTROPANE DERIVATIVE; SILVER; TRANS 1,4 DITOSYLOXY 2 BUTENE; TRANS 4 BROMO 1 TOSYLOXY 2 BUTENE; TRANS 4 FLUORO 1 TOSYLOXY 2 BUTENE; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; CIS ISOMER; HYDROLYSIS; ISOTOPE LABELING; NUCLEOPHILICITY; POSITRON EMISSION TOMOGRAPHY; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION TIME; SYNTHESIS;

EID: 84932196195     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2015.05.100     Document Type: Article

References (20)

1. P. Chen, C.D. Kilts, V.M. Camp, T.D. Ely, R. Keil, E. Malveaux, J. Votaw, J.M. Hoffman, and M.M. Goodman J. Labelled Compd. Radiopharm. 42 1999 S400
2. F. Dollé, P. Emond, S. Mavel, S. Demphel, F. Hinnen, Z. Mincheva, W. Saba, H. Valette, S. Chalon, C. Halldin, J. Helfenbein, J. Legaillard, J.-C. Madelmont, J.-B. Deloye, M. Bottlaender, and D. Guilloteau Bioorg. Med. Chem. 14 2006 1115 1125
3. J.S. Stehouwer, L.M. Daniel, P. Chen, R.J. Voll, L. Williams, S.J. Plott, J.R. Votaw, M.J. Owens, L. Howell, and M.M. Goodman J. Med. Chem. 53 2010 5549 5557
4. Goodman, M. M.; Chen, P. WO 2000064490 A1, 2000.
5. F. Dollé, F. Hinnen, P. Emond, S. Mavel, Z. Mincheva, W. Saba, M.-A. Schöllhorn-Peyronneau, H. Valette, L. Garreau, S. Chalon, C. Halldin, J. Helfenbein, J. Legaillard, J.-C. Madelmont, J.-B. Deloye, M. Bottlaender, and D. Guilloteau J. Labelled Compd. Radiopharm. 49 2006 687 698
6. F. Dollé, J. Helfenbein, F. Hinnen, S. Mavel, Z. Mincheva, W. Saba, M.-A. Schöllhorn-Peyronneau, H. Valette, L. Garreau, S. Chalon, C. Halldin, J.-C. Madelmont, J.-B. Deloye, M. Bottlaender, J. Le Gailliard, D. Guilloteau, and P. Emond J. Labelled Compd. Radiopharm. 50 2007 716 723
7. W.D. Emmons, and A.F. Ferris J. Am. Chem. Soc. 75 1953 2257
8. H.M.R. Hoffmann J. Chem. Soc. 1965 6748 6753
9. G.S. Hammond, M.F. Hawthorne, J.H. Waters, and B.M. Graybill J. Am. Chem. Soc. 82 1960 704 711
10. Stehouwer, J. S.; Birnbaum, M. S.; Voll, R. J.; Owens, M. J.; Plott, S. J.; Bourke, C. H.; Wassef, M. A.; Kilts, C. D.; Goodman, M. M. 2015, Unpublished results.
11. Asuma, Y.; Suzuki, T.; Hidaka, T.; Asada, K.; Miyake, R.; Dekishima, Y.; Kawabata, H. US 2013/0096339 A1; PCT/JP2011/053285, 2013.
12. G.A. Edwards, P.A. Culp, and J.M. Chalker Chem. Commun. 2015 515 518
13. A.E.G. Miller, J.W. Biss, and L.H. Schwartzman J. Org. Chem. 24 1959 627 630
14. M.G. Organ, J.T. Cooper, L.R. Rogers, F. Soleymanzadeh, and T. Paul J. Org. Chem. 65 2000 7959 7970
15. R.A. Raphael J. Chem. Soc. 1952 401 405
16. S. Bouquillon, and J. Muzart Eur. J. Org. Chem. 2001 3301 3305
17. C. Malanga, L. Pagliai, and R. Menicagli Synth. Commun. 20 1990 2821 2826
18. M. Kinoshita, H. Takami, M. Taniguchi, and T. Tamai Bull. Chem. Soc. Jpn. 60 1987 2151 2161
19. P. Casara, P. Marchal, J. Wagner, and C. Danzin J. Am. Chem. Soc. 111 1989 9111 9113
20. L.-W. Hsin, E.L. Webster, G.P. Chrousos, P.W. Gold, W.C. Eckelman, C. Contoreggi, and K.C. Rice J. Labelled Compd. Radiopharm. 43 2000 899 90